The Chesapeake Bay (CB) basin is under a total maximum daily load (TMDL) mandate to reduce nitrogen, phosphorus, and sediment loads to the bay. Identifying shifts in the hydro-climatic regime may help explain observed trends in water quality. To identify potential shifts, hydrologic data (1927–2014) for 27 watersheds in the CB basin were analyzed to determine the relationships among long-term precipitation and stream discharge trends. The amount, frequency, and intensity of precipitation increased from 1910 to 1996 in the eastern U.S., with the observed increases greater in the northeastern U.S. than the southeastern U.S. The CB watershed spans the north-to-south gradient in precipitation increases, and hydrologic differences have been observed in watersheds north relative to watersheds south of the Pennsylvania—Maryland (PA-MD) border. Time series of monthly mean precipitation data specific to each of 27 watersheds were derived from the Precipitation-elevation Regression on Independent Slopes Model (PRISM) dataset, and monthly mean stream-discharge data were obtained from U.S. Geological Survey streamgage records. All annual precipitation trend slopes in the 18 watersheds north of the PA-MD border were greater than or equal to those of the nine south of that border. The magnitude of the trend slopes for 1927–2014 in both precipitation and discharge decreased in a north-to-south pattern. Distributions of the monthly precipitation and discharge datasets were assembled into percentiles for each year for each watershed. Multivariate correlation of precipitation and discharge within percentiles among the groups of northern and southern watersheds indicated only weak associations. Regional-scale average behaviors of trends in the distribution of precipitation and discharge annual percentiles differed between the northern and southern watersheds. In general, the linkage between precipitation and discharge was weak, with the linkage weaker in the northern watersheds compared to those in the south. On the basis of simple linear regression, 26 of the 27 watersheds are projected to have higher annual mean discharge in 2025, the target date for implementation of the TMDL for the CB basin.